| Sport | Date | Teams | Location | Time |
| Girls Soccer | Sep 03 | Lenox at Pittsfield | BCC | 07:00 PM |
| |
| Boys Soccer | Sep 04 | Chicopee at Pittsfield | | 04:30 PM |
| |
| Girls Soccer | Sep 05 | Pittsfield at Mount Greylock | | 04:30 PM |
| |
| Boys Soccer | Sep 06 | Mount Greylock at Pittsfield | BCC | 06:00 PM |
| |
| Girls Soccer | Sep 09 | Pittsfield at Mount Everett | | 04:30 PM |
| |
| Boys Soccer | Sep 10 | Pittsfield at Wahconah | | 07:00 PM |
| |
| Girls Soccer | Sep 11 | Pittsfield at Chicopee Comp | | 04:30 PM |
| |
| Boys Soccer | Sep 13 | Pittsfield at Minnechaug | | 04:00 PM |
| Football | Sep 13 | Pittsfield at Wahconah | | 07:00 PM |
| |
| Girls Soccer | Sep 14 | Taconic at Pittsfield | | 01:00 PM |
| |
| Boys Soccer | Sep 16 | Longmeadow at Pittsfield | | 04:30 PM |
| |
| Girls Soccer | Sep 17 | W. Springfield at Pittsfield | | 04:30 PM |
| |
| Boys Soccer | Sep 18 | Shepherd Hill at Pittsfield | | 05:00 PM |
| |
| Boys Soccer | Sep 20 | Lenox at Pittsfield | | 04:00 PM |
| |
| Football | Sep 21 | Northampton at Pittsfield | BCC | 07:00 PM |
| |
| Girls Soccer | Sep 23 | Pittsfield at Monument Mountain | | 06:00 PM |
| |
| Girls Soccer | Sep 25 | Hoosac Valley at Pittsfield | | 04:30 PM |
| |
| Boys Soccer | Sep 26 | Monument Mountain at Pittsfield | | 04:30 PM |
| |
| Football | Sep 27 | Pittsfield at Lee | | 07:00 PM |
| |
| Boys Soccer | Sep 28 | Pittsfield at W. Springfield | | 07:00 PM |
| |
| Girls Soccer | Oct 03 | Wahconah at Pittsfield | BCC | 07:00 PM |
| |
| Boys Soccer | Oct 04 | Pittsfield at Mount Greylock | | 07:00 PM |
| Football | Oct 04 | S. Hadley at Pittsfield | BCC | 07:00 PM |
| |
| Boys Soccer | Oct 05 | Hoosac Valley at Pittsfield | | 01:00 PM |
| |
| Boys Soccer | Oct 07 | Wahconah at Pittsfield | BCC | 06:30 PM |
| Girls Soccer | Oct 07 | Mount Greylock at Pittsfield | Kirvin Park | 04:30 PM |
| |
| Girls Soccer | Oct 10 | Hoosac Valley at Pittsfield | | 04:00 PM |
| |
| Football | Oct 11 | W. Springfield at Pittsfield | BCC | 07:00 PM |
| Girls Soccer | Oct 11 | Pittsfield at Belchertown | | 04:00 PM |
| |
| Boys Soccer | Oct 12 | Pittsfield at Taconic | BCC | 11:00 AM |
| |
| Girls Soccer | Oct 13 | Pittsfield at Taconic | BCC | 01:00 PM |
| |
| Girls Soccer | Oct 17 | Pittsfield at Hoosac Valley | | 04:30 PM |
| |
| Boys Soccer | Oct 18 | Pittsfield at Lenox | | 06:00 PM |
| Football | Oct 18 | Pittsfield at Amherst | | 07:00 PM |
| Girls Soccer | Oct 18 | Pittsfield at Drury | | 04:00 PM |
| |
| Boys Soccer | Oct 19 | Pittsfield at Southwick | | 02:00 PM |
| |
| Boys Soccer | Oct 21 | Pittsfield at Ludlow | | 04:30 PM |
| |
| Girls Soccer | Oct 22 | Pittsfield at Springfield Central | | 04:00 PM |
| |
| Boys Soccer | Oct 25 | Pittsfield at Monument Mountain | | 06:00 PM |
| Football | Oct 25 | Putnam at Pittsfield | BCC | 06:00 PM |
| Girls Soccer | Oct 25 | Monument Mountain at Pittsfield | | 04:15 PM |
| |
| Girls Soccer | Oct 28 | Pittsfield at Wahconah | | 04:30 PM |
| |
| Boys Soccer | Oct 29 | Pittsfield at Shepherd Hill | | 06:00 PM |
| |
| Football | Nov 01 | Pittsfield at Taconic | BCC | 06:30 PM |
